Sean, is Jack & Jills still open in Brewster?
jrackman:
Yes they are! And Steve P. still owns and runs the place. On Sundays starting at 2:00pm, they still have their handicapped 9-ball tourney with calcutta, that top local talent (e.g. Elder Jesus, Yassie Ramirez -- "AA" and "AAA" players) are tough to beat, even with a stiff handicap working against them. Once in a great while (we're talking "blue moon"), Jeremy Sossei stops in as well. Same impeccably-maintained Gold Crown 1s that the place started with way back in the early 1960s. They also have a Gold Crown IV in the front of the room that's used for semi-finals and finals matches in tournaments. And table 14 is still the tightest-pocketed table in the place -- 4" pockets. Excellent home-cooked meals from their kitchen (and not bar fodder, either -- full-course meals -- some of the tastiest-prepared meals I've ever had in a pool hall).
The single barbox they have is a Valley Cougar, though; not a Diamond like you asked for. There's also a Sorenson 3C billiards table that gets occasional action.
I don't play there as often as I do at, say Iron Willies, or Busters Billiards & Amusements (in New Milford, CT -- Jeremy S. is occasionally there as well). The reason is that folks there only want to play fast rotation games. You walk in there and say that you want to play a game of pool with someone, and you instantly get a diamond-shaped rack of balls racked for you. Only Steve P. and a very few sparse old-timers will engage you in, say, a set of One Pocket or 14.1, or even 3C billiards.
The other places I mentioned have a greater number of players with expanded horizons (i.e. they know of games other than that "diamond-shaped rack" game).
Hope this helps, and yes, do let me know if you're in the area! Jack and Jills in Brewster is great, because it's so close to me (I'm in the next town over, Carmel).
-Sean